A New Synthesis of Neu5Ac from d-Glucono-δ-lactone
Authors:
- 28 August 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (19) , 6758-6763
Abstract
A new route to Neu5Ac methyl ester (23) with a readily available sugar d-glucono-δ-lactone as starting material has been developed. A diastereoselective propargylation of α-acetamino aldehyde and a subsequent KMnO4 oxidation of the terminal alkyne served as the key steps.Keywords
This publication has 11 references indexed in Scilit:
- An efficient method for synthesis of α-keto acid esters from terminal alkynesTetrahedron Letters, 2002
- Recent Advances in the Synthesis of Sialic Acid Derivatives and Sialylmimetics as Biological ProbesChemical Reviews, 2002
- Synthesis of a Six-Carbon Sialic Acid Using an Indium-Mediated CouplingOrganic Letters, 2000
- Enzyme action in glycoprotein synthesisCellular and Molecular Life Sciences, 1998
- Diastereoselective Propargylation of .alpha.-Alkoxy Aldehydes with Propargyl Bromide and Zinc. A Versatile and Efficient Method for the Synthesis of Chiral Oxygenated Acyclic Natural ProductsThe Journal of Organic Chemistry, 1995
- Enzymes in carbohydrate synthesis: N-acetylneuraminic acid aldolase catalyzed reactions and preparation of N-acetyl-2-deoxy-D-neuraminic acid derivativesJournal of the American Chemical Society, 1988
- Synthesis of 1,5-lactones of 3-deoxy-d-manno-2-octulopyranosonic acid (KDO)Carbohydrate Research, 1988
- A new synthesis ofN-acetylneuraminic acidHelvetica Chimica Acta, 1988
- The chemistry of D‐gluconic acid derivatives. Part 1: Synthesis of 3,4;5,6‐di‐O‐isopropylidene‐D‐glucitol and 2,3;4,5‐di‐O‐isopropylidene‐aldehydo‐D‐arabinose from D‐glucono‐1,5‐lactoneRecueil des Travaux Chimiques des Pays-Bas, 1987
- Zur Konformation der N‐Acetyl‐neuraminsäureEuropean Journal of Inorganic Chemistry, 1968